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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 324337Generated: October 27, 2026

Acetone → 2,5-Dicarbamoylbenzoic acid

https://huagongshe.com/reaction/324337

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetoneHCID 180—
ReactantAmmoniaHCID 222—
Reactant1,2,4-Benzenetricarbonyl trichlorideHCID 77472—
Reactant4-CarbamoylphthalimideHCID 10679219—
SolventChloroformHCID 6212—
SolventDichloromethaneHCID 6344—
SolventEthyl AcetateHCID 8857—
Product2,5-Dicarbamoylbenzoic acidHCID 19805153—
Product2,4-Dicarbamoylbenzoic acidHCID 22004420—

Reaction Steps

In this step, 4-carbamoylphthalimide is prepared by reacting trimellitoyl chloride with ammonia and dehydrating the obtained product. Specifically, this reaction is conducted by reacting trimellitoyl chloride with aqueous ammonia either without any solvent or in a state dissolved in a solvent at a temperature ranging from about −15° C. to room temperature. The solvent to be used in this case is preferably acetone, dichloromethane, chloroform or ethyl acetate, though any organic solvent inert to the reaction may be used. The resulting reaction mixture is treated with an acid to give a mixture comprising 2,4-dicarbamoylbenzoic acid and 2,5-dicarbamoylbenzoic acid. This mixture is further treated in the absence or presence of a solvent for 0.5 to 24 hours to give the objective compound. This treatment is conducted at room temperature to about 200° C. The solvent to be used in this treatment is preferably N-methyl-2-pyrrolidinone, though any solvent inert to the reaction may be used.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06218392B1
Source datasetuspto-grants-2001_04
ORD IDord-00cc83933e0b467ba81d48950385e60d
Source noteuspto-grants-2001_04